Highly Rated Hotels With Pool in Stockbridge

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Our top choices for Stockbridge hotels with a pool

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

$191 nightly

Jun 22 - Jun 23

Total with taxes and fees

Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.

$358 nightly

Jun 24 - Jun 25

Total with taxes and fees

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

$108 nightly

Jun 15 - Jun 16

Total with taxes and fees

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

$88 nightly

Jun 11 - Jun 12

Total with taxes and fees

Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

$152 nightly

Jun 11 - Jun 12

Total with taxes and fees

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

$135 nightly

Jun 14 - Jun 15

Total with taxes and fees

Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Lenox

Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.

$135 nightly

Jun 29 - Jun 30

Total with taxes and fees

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

$164 nightly

Jun 11 - Jun 12

Total with taxes and fees

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Breakfast included

Hot tub

Top Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Everything was good but restaurant need to close later. Parking was an issue."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The view was great. It is in 10 to 30 minutes of places I wanted to visit. The staff went out of their way to accommodate me with the personal items I needed. I didn't need to use the Kayaks or pontoon that they rent to use on Lake Laural. The only drawback is no beach."

The Red Lion Inn

8/10 Good

"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."

Vacation Village in the Berkshires

10/10 Excellent

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent value for the money. Friendly staff. I got a one-bdrm condo for the price of a standard hotel. No grocery atores nearby some come with supplies if you plan to cook."

The Yankee Inn

10/10 Excellent

"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."

Frequently asked questions

What are the best hotels in Stockbridge with outdoor pools?

The Red Lion Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, great for families looking to unwind after a day of adventure in the beautiful Berkshires. Guests rave about the comfortable and quiet rooms, as well as the excellent food and friendly service provided by the staff. Plus, its prime location in a historic district means you're just a stone's throw away from local attractions, including nearby ski areas for winter sports enthusiasts.

For a more intimate experience, consider The Stockbridge Country Inn, rated 4.5 stars by travellers. This delightful bed and breakfast not only features an outdoor pool but also provides complimentary full and continental breakfasts, ensuring a great start to your day. With its proximity to the Norman Rockwell Museum and picturesque mountain views, it's an ideal spot for families seeking both relaxation and cultural enrichment. Guests particularly appreciate the peaceful atmosphere and the opportunity for mountain biking right on-site.

How much does a hotel with outdoor pool in Stockbridge cost?

Enjoy staying in a hotel in Stockbridge with an outdoor pool. You can find a great deal from $82 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Is it cheaper to book flights and a Stockbridge hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

How can I save on a Stockbridge hotel with a pool with Expedia?

Before booking your Stockbridge hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Stockbridge for you.

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Check availability on Stockbridge Hotels with a Pool

Our top choices for Stockbridge hotels with a pool

The Red Lion Inn

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Yankee Inn

The Little Lion

Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hampton Inn & Suites Berkshires-Lenox

Blackberry River Inn

The Springs Motel

Howard Johnson by Wyndham Lenox

Choose what matters most at hotels with a pool in Stockbridge

Top Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Red Lion Inn

Vacation Village in the Berkshires

The Yankee Inn

Hampton Inn & Suites Berkshires-Lenox

Quality Inn Great Barrington

Courtyard by Marriott Lenox Berkshires

Frequently asked questions

Explore a world of travel with Expedia

Find Hotels with a Pool in Stockbridge, MA

Upfront pricing

Treat yourself

Be picky

Check availability on Stockbridge Hotels with a Pool

Our top choices for Stockbridge hotels with a pool

The Red Lion Inn

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Yankee Inn

The Little Lion

Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hampton Inn & Suites Berkshires-Lenox

Blackberry River Inn

The Springs Motel

Howard Johnson by Wyndham Lenox

Choose what matters most at hotels with a pool in Stockbridge

Top Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

Explore a world of travel with Expedia